Ring-opening reactions of 2-benzoylcyclopropane isocyanate

Abstract

triturated with methylene chloride. Evaporation of the methylene chloride left a residue of 1.34 g. This was heated at 170°until cessation of gas evolution (~30 min). The crude mixture of amino monoacids (1.0 g) was dissolved in 10 ml of absolute ethanol, saturated with HC1, and heated under reflux overnight. Neutralization with aqueous KOH followed by extraction with ether gave 0.70 g (62%) of amino ester mixture 5 and 6.Chromatography of 250 mg of this mixture on 10 g of Florisil gave 27 mg of essentially pure 5 (eluted with 1:1 ether-hexane): X (CC14) 3.58, 5.78, 8.50, 9.66 µ; r (CC14) 5.97 (2 H, q, J = 7 Hz), 7.3-9.4 (21 H, m, containing t at 8.77, J = 7 Hz); m/e 213 (parent), 84 (base peak).

Diaryldiamines with Dual Inhibition of the Histamine H3 Receptor and the Norepinephrine Transporter and the Efficacy of 4-(3-(Methylamino)-1-phenylpropyl)-6-(2-(pyrrolidin-1-yl)ethoxy)naphthalen-1-ol in Pain

“…tert-Butyl 4-(4-Hydroxyphenyl)-4-phenylbutyl(methyl)carbamate (23). Compound 21 30 (65 mg, 0.36 mmol) and phenol (102 mg, 1.09 mmol) via the procedure for 22, Step 1, provided a mixture of 4-(4-(methylamino)-1-phenylbutyl)phenol and 2-(4-(methylamino)-1-phenylbutyl)phenol. This mixture of was treated with Boc 2 O (38 mg, 0.17 mmol) in CH 3 CN (2 mL), heated for 2 min at reflux, cooled, concentrated, and directly chromatographed, eluting with a gradient of 1:1 to 0:1 hexane/[9:1 CH 2 Cl 2 /EtOAc] to provide 23 as the more polar isomer.…”